The goals of this study are to identify factors influencing the intention of high-school students across Taiwan Straits to participate in the Web-based Distance Education (DE). MISS (Multi-faceted Internet Survey System) has been adopted to collect data from 3,677 high-school students from both China and Taiwan. All indicators of this study, such as the availability of school online courses, home computer environment, high-school student computer skills and also their practical experiences in taking online courses, are re-constructed based on each indicator?s own set of variables in order to evaluate their impacts on high-school students? willingness to take Web-based DE courses in the future. Estimations of logistic regression models of high-school students in China and Taiwan respectively are generated to predict factors influencing their intentions to take DE courses on the Web. Finally, policy oriented recommendations on how to enhance high-school students? intention to participate in the Web-based DE are suggested.